American Chemical Society
ol0c00666_si_001.pdf (2.49 MB)

1,2,6-Thiadiazine 1‑Oxides: Unsaturated Three-Dimensional S,N-Heterocycles from Sulfonimidamides

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journal contribution
posted on 2020-03-13, 20:44 authored by Jan-Hendrik Schöbel, Marco Thomas Passia, Nadja Anna Wolter, Rakesh Puttreddy, Kari Rissanen, Carsten Bolm
Unprecedented three-dimensional 1,2,6-thiadiazine 1-oxides have been prepared by an aza-Michael-addition/cyclization/condensation reaction sequence starting from sulfonimidamides and propargyl ketones. The products have been further functionalized by standard cross-coupling reactions, selective bromination of the heterocyclic ring, and conversion into a β-hydroxy substituted derivative. A representative product was characterized by single-crystal X-ray structure analysis.